Do You Want To Get Rich Selling? Well Do Ya Pal?


LinkedIn is the user interface for mediocre sales talent to reposition as a SALES GURU or Sherpa who can teach “sales hacks” enabling new-to-sales types to find wealth, happiness and everlasting personal fulfillment.

You can bet it is all BULL. 

If those charlatans on LinkedIn, jumping up and down on stage, pix with audiences of the hundreds in front of them, blue hair, mohawk haircuts doing COLD CALLING seminars had been successful they would not be on LinkedIn selling advice to kids.

Reality 1: Anyone selling sales advice on LinkedIn has not been wildly successful. If they had been, they would not have to sell sales advice to strangers.

So, do you want to know the secret to getting rich selling? Well, do you pal?

First, let’s agree on what getting rich is all about. It is about economic independence. That means you can live your life the way you want to, donate your time to your dreams, help injured animals or travel the world and not sleep in youth hostels.

Whatever it is to you, economic independence is its foundation. Without economic independence, you still have to come up for air, become a barista, work that crappy dial-for-dollars gig, and have to take orders from someone half your age, someday, in a job you loathe.

If you are NOT interested in a sales career that may give you true financial independence, that’s cool. Stop reading and get back to the clichés from life coaches, posted every day on LinkedIn and Facebook.

Are you still here?

Reality 2: If you are not selling stuff that matters, that has a significant price point, you cannot make commissions that will set you free.

While this should be obvious, it isn’t. We speak to people doing BDR work (kids who dial for dollars, inside sales, first sales gig) passing leads to “senior reps.” OK, you are never going to get there doing BDR work. If you are good, you keep doing it. If you suck, you get fired. Either way, you are pretty much screwed financially.

You have to be in front of the customer as the salesperson.

You have to sell STUFF THAT MATTERS!

If your company sells transaction level products, unit price less than $250,000 MINIMUM per sale, you are in the transaction world. That is SALES DEATH.

If you are that person selling transaction level products, to low level cubicle dwellers, there is no way you can ever generate enough rev so that you make real dough. 

Think Chef, Puppet, XebiaLabs, LogDNA, almost every security software product and about 99% of the stuff you see on LinkedIn.

Reality 3: If there are a dozen firms doing what your company does, you cannot break through the noise. Crowded markets mean you will fail.

Your marketing department will tell you your DevOps, security, social media or NoSQL product is totally different from all the competitors. Just go out there and sell the heck out of it. Get that message to the buyer and she will get it.

And that is nonsense. The other 11 companies who do what you generally do in your category all have over-amped-up marketing types who spend days on some differentiator so minuscule nobody pays attention to it. Their job is to create differentiation – even when it is not appreciably there. You are screwed trying to sell nonsense the customer will never get. 

Move on!

Reality 4: Stock options are more likely to screw you than to make you financially independent.

Stock options sound great. There are plenty of people who achieved financial independence with them. That was THEN. YOU are in NOW.

Stock options are usually for VC financed companies. They are very often on the C, D, E or X round. Every round means your options are worth about 30% less.

If you think you are going to make some option dough, ask this question at the smarmy weekly company meeting: “How much is one option worth today on a fully diluted basis.”

Ask it! I dare you!

Reality 5: There are companies and products that can make you financially independent, and they are looking for you.

The B2B tech sector is filled with about 98% of current sales reps who NEED a big salary, large marketing budget, generated “leads.” Each rep has a nice comfortable expense account.

You know them. They work for Dell, VMware, SAP, Oracle or a host of other places where all you need is an order pad and and a pen.

They never make big money on a continual basis. That is because the money goes into the infrastructure, not commission.


Try working for an up-and-comer where you can create some basic marketing material for your own deals. You can generate your own leads. You can get in front of customers (not that hard if you pay attention to Reality 3, above).

There are all kinds of small companies who will give you a much more leveraged comp plan where you get paid real dough if you produce.

Is it harder? Not really.

It is different. You do not have the leads on your desk every morning. Sales reps today will tell you those marketing leads suck anyway, they are a waste.

You don’t get a big base. Right. Big base salaries are for people who need them. Stay lean when you start and you get the big comp. Big comp = financial independence. Big base = mediocre sales types.

Reality 6: Quit Often. Go where the dough is. You will be LIED TO!

You will hear nonsense that you need to be in a sales job 3-5 years. You do not want to be a job hopper. You should not be perceived as someone who leaves one job for the next one. No loyalty.

That is the kind of HR crap the “we have a great, nurturing culture” types tell you and it is indeed, a load of BULL.

When you are interviewing, the Sales VP, who will be replaced every 18 months, will say anything if she wants you. Everything is great; the last 4 guys who left just didn’t call high enough.

Right! Neither will you. If you find yourself, after those first 45 days, asking how it is you ever joined this lousy place, where nothing seems to work, the strategies are changed monthly, the web site every quarter and you are stuck in QBRs, get out!

Your TIME is your most important resource. Most of these over VC-funded SaaS/B2B/software companies are the living dead. They will never make real money; the options are toast.

You may be 30ish now but you will someday be 55 or 60. Imagine being 55, with a mortgage, 2 kids in college, spouse does not work, three nice cars. 

Your pal the Sales VP gets fired. The new VP, 28 years old comes in and starts bringing in all their pals from the last gig.

You know where this is going don’t you. Make dough NOW! Tomorrow is TOO LATE!

There is NO INSTITUTIONAL MEMORY in B2B sales. Take the crappy place off your resume or LinkedIn profile and use their base to support yourself while you find a real job. Get OUT!

Reality 7: Your ability to succeed is inversely proportional to the size of the sales force.

If you only have a high school degree or you went to a college with the name of an ocean in it, or have a degree in communications, that means big sales forces drive everyone to sell the same way. Selling the same way means nobody succeeds wildly; everyone kind of does OK.

If there are more than a dozen sales reps, you ain’t likely to make big dough. 

Be early, innovative, aggressive. None of this is possible within a large sales force.

Reality 8: Innovators and early adopters are looking for you. Find them.

If you are still reading here, you understand you need to sell an early, innovative, unique product. They are out there and need people to find their market. That’s you.

All the sales training on LinkedIn and other sources of mediocrity and clichés train to sell to the late market. Almost all training is aimed at how to sell when you are in front of the customer, at her desk.

Well, nobody is getting to that desk. 80% of sales reps do not make quota. 

There are people who do buy, who do innovate and who can bring you into deals that are so significant you achieve independent wealth – to open that animal shelter. Sell to the innovator or early adopter.

If your product is NOT something the innovator is seeking, you have, by definition found a place you should QUIT NOW! See Reality 6. 

Reality 9: Sell to the customer the way they want to buy.

OK, our first sales cliché! 

But we mean something different people. Stay with us here.

There is this paradox in sales that when someone is a human being, we know how to talk to them. When they are a prospective customer, everything falls apart.

They are a “prospect.” They are at the “top of the funnel.” If they respond to anything, they are a “lead.”

The fact they are a person has been long lost.

Sell to the buyer the way YOU want to buy.

Do you take phone calls from strangers, with blue hair or a mohawk haircut “pitching” you in a cold call?

Or do you chat with your buds about an important purchase and see if they have advice?

Think through concepts like trusted advisor selling. It works every time and it is NOT what the sales gurus tell you it is.

YOU cannot be the trusted advisor. Nor can some EXPERT at your firm.